US4072726A
Expired / Lapsed
US
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Hydrogenation of fluorinated esters
Assignee: Honeywell International Inc
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Filing: 1977-01-21
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Granted: 1978-02-07
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Expires: 1997-01-21
Abstract
Abstract Fluorinated esters of the formula CnHxF2n+1-x CO2CH2CmHyF2m+1-y such as CF3CO2CH2CF3 are hydrogenated to fluorinated alcohols such as CF3CH2OH using a catalyst having between 50 and 100 percent, and preferably 75-95 percent CuO by weight. In the above formula n= 1 to 13, m= 1 to 13, x= 0 to 3 and y= 0 to 3. In the most preferred esters, n= m and x= y= 0. The catalyst may also contain 0-50 percent and preferably 5-25 percent by weight of a filler or binder such as a silicate salt. The reaction produces greater yields of alcohol and longer catalyst life than with chromite catalysts, and may proceed at substantially atmospheric pressures.
Inventors
- 👤 Henry R. Nychka
- 👤 Richard E. Eibeck
- 👤 Martin A. Robinson
- 👤 Edward S. Jones
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 09:30
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/147; C07C29/149
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
135 words
A method for the preparation of fluorinated alcohols of the formula C n H x F 2n+1-x CH 2 OH, wherein n=1 to 13 and x=0 to 3 but not more than n, comprising passing at between about 200° C and about 325° C a vaporous mixture of hydrogen and a fluorinated ester of the formula C n H x F 2n+1-x CO 2 CH 2 -- C m H y F 2m+1-y , wherein n and x are as described above and m=1 to 13 and y=0 to 3 but not more than m, over a catalyst consisting essentially of about 50 to 100 percent by weight CuO and 0 to about 50 percent by weight of an inert base or binder, said catalyst being essentially free of chromite, and recovering the fluorinated alcohol.
Claim 2
Independent Claim
135 words
A method for the preparation of fluorinated alcohols of the formula C n H x F 2n+1-x CH 2 OH, wherein n=1 to 13 and x=0 to 3 but not more than n, comprising passing at between about 200° C and about 325° C a vaporous mixture of hydrogen and a fluorinated ester of the formula C n H x F 2n+1-x CO 2 CH 2 -- C m H y F 2m+1-y , wherein n and x are as described above and m=1 to 13 and y=0 to 3 but not more than m, over a catalyst consisting essentially of about 50 to 100 percent by weight CuO and 0 to about 50 percent by weight of an inert base or binder, said catalyst being essentially free of chromite, and recovering the fluorinated alcohol.
Claim 3
Dependent Claim
25 words
A method as claimed in claim 1 wherein the fluorinated ester is passed over the catalyst for about 1 to about 20 seconds contact time.
Claim 4
Dependent Claim
25 words
A method as claimed in claim 1 wherein the fluorinated ester is passed over the catalyst at between about 225° C and about 275° C.
Claim 5
Dependent Claim
20 words
A method as claimed in claim 2 wherein the contact time is between about 3 seconds and about 10 seconds.
Claim 6
Dependent Claim
19 words
The method as claimed in claim 1 wherein the inert base is the silicate salt of an alkali metal.
Claim 7
Dependent Claim
17 words
The method as claimed in claim 5 wherein the silicate salt is Na 2 SiO 3 .
Claim 8
Dependent Claim
53 words
The method as claimed in claim 1 wherein the fluorinated ester is the ester of a fluorinated acid and a similarly fluorinated alcohol, said acid and alcohol having the same number of carbons, with n=m and x=y, whereby the effluent contains as organic materials only unreacted fluorinated ester and an homogenous alcohol product.
Claim 9
Dependent Claim
9 words
The method as claimed in claim 1 wherein x=y=0.
Claim 10
Dependent Claim
9 words
The method as claimed in claim 8 wherein n=m.
Claim 11
Dependent Claim
21 words
The method as claimed in claim 9 wherein the fluorinated ester is CF 3 CO 2 CH 2 CF 3 .
Claim 12
Dependent Claim
22 words
The method as claimed in claim 1 wherein the molar ratio of hydrogen to ester is between about 2.0:1 and about 4.0:1.
Claim 13
Dependent Claim
31 words
The method as claimed in claim 1 wherein the catalyst contains by weight about 75 to about 95 percent CuO and about 5 to about 25 percent inert base, by weight.
Claim 14
Dependent Claim
30 words
The method as claimed in claim 1 further including the steps of separating the unreacted fluorinated ester from the fluorinated alcohol product by distillation and reintroducing the unreacted fluorinated ester.
Claim 15
Dependent Claim
39 words
The method as claimed in claim 1 wherein the byproduct C m H y F 2m+1-y CH 2 OH is recovered and reacted with the acid chloride C n H x F 2n+1-x COCl to form the fluorinated ester.
Claim 16
Dependent Claim
42 words
The method as claimed in claim 7 wherein a portion of the C n H x F 2n+1-x CH 2 OH homogeneous alcohol product is reacted with the acid chloride C n H x F 2n+1 COCl to form the fluorinated ester.
Claim 17
Dependent Claim
17 words
The method as claimed in claim 1 wherein the hydrogenation reaction is conducted at substantially atmospheric pressure.
Claim 18
Dependent Claim
21 words
The method as claimed in claim 2 wherein said fluorinated ester is CF 3 CO 2 CH 2 CF 3 .
Claim 19
Dependent Claim
19 words
The method of claim 12 wherein said fluorinated ester is CF 3 CO 2 CH 2 CF 3 .
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-02-06 | 1981-08-08 | 1982-02-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-06 | 1985-08-08 | 1986-02-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-06 | 1989-08-08 | 1990-02-07 | $7700.00 | Window Closed / Lapsed |